Mapping the regioisomeric distribution of fatty acids in triacylglycerols by hybrid mass spectrometry

Journal of Lipid Research

Volumn 54, Issue 1, 2013, Pages 290-305

  Nagy, Kornél ^a   Sandoz, Laurence ^a   Destaillats, Fréd́eric ^a   Schafer, Olivier ^a  

^a NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

Fatty acid; Lipidomics; Nutrition; Triglycerides

Indexed keywords

FATTY ACID; TRIACYLGLYCEROL;

ACCURACY; ARTICLE; CALIBRATION; CHROMATOGRAPHY; HYBRID MASS SPECTROMETRY; IONIZATION; ISOMER; LIMIT OF DETECTION; LIMIT OF QUANTITATION; MASS SPECTROMETRY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REGIOISOMER;

CALIBRATION; CHROMATOGRAPHY, REVERSE-PHASE; FATTY ACIDS; MASS SPECTROMETRY; OILS; REPRODUCIBILITY OF RESULTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TRIGLYCERIDES;

EID: 84871182146     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.D031484     Document Type: Article

References (68)

1. Murphy, R. C., P. F. James, A. M. McAnoy, J. Krank, E. Duchoslav, and R. M. Barkley. 2007. Detection of the abundance of diacylglycerol and triacylglycerol molecular species in cells using neutral loss mass spectrometry. Anal. Biochem. 366: 59-70. (Pubitemid 46779007)
2. McAnoy, A. M., C. C. Wu, and R. C. Murphy. 2005. Direct qualitative analysis of triacylglycerols by electrospray mass spectrometry using a linear ion trap. J. Am. Soc. Mass Spectrom. 16: 1498-1509. (Pubitemid 41169859)
3. Neville, M. C., and M. F. Picciano. 1997. Regulation of milk lipid secretion and composition. Annu. Rev. Nutr. 17: 159-183.
4. Lisa, M., H. Velinska, and M. Holcapek. 2009. Regioisomeric characterization of triacylglycerols using silver-ion HPLC/MS and randomization synthesis of standards. Anal. Chem. 81: 3903-3910.
5. Lisa, M., K. Netusilova, L. Franek, H. Dvorakova, V. Vrkoslav, and M. Holcapek. 2011. Characterization of fatty acid and triacylglycerol composition in animal fats using silver-ion and non-aqueous reversed-phase high-performance liquid chromatography/mass spectrometry and gas chromatography/flame ionization detection. J. Chromatogr. A. 1218: 7499-7510.
6. Hunter, J. E. 2001. Studies on effects of dietary fatty acids as related to their position on triglycerides. Lipids. 36: 655-668. (Pubitemid 32777010)
7. Mu, H., and T. Porsgaard. 2005. The metabolism of structured triacylglycerols. Prog. Lipid Res. 44: 430-448. (Pubitemid 41613755)
8. Redgrave, T. G., D. R. Kodali, and D. M. Small. 1988. The effect of triacyl-sn-glycerol structure on the metabolism of chylomicrons and triacylglycerol-rich emulsions in the rat. J. Biol. Chem. 263: 5118-5123.
9. Ramírez, M., L. Amate, and A. Gil. 2001. Absorption and distribution of dietary fatty acids from different sources. Early Hum. Dev. 65 (Suppl.): S95-S101.
10. Rogalska, E., S. Ransac, and R. Verger. 1990. Stereoselectivity of lipases. II. Stereoselective hydrolysis of triglycerides by gastric and pancreatic lipases. J. Biol. Chem. 265: 20271-20276. (Pubitemid 120014006)
11. Rogalska, E., C. Cudrey, F. Ferrato, and R. Verger. 1993. Stereoselective hydrolysis of triglycerides by animal and microbial lipases. Chirality. 5: 24-30. (Pubitemid 23123047)
12. Mattson, F. H., and R. A. Volpenhein. 1964. The digestion and absorption of triglycerides. J. Biol. Chem. 239: 2772-2777.
13. Beermann, C., N. Winterling, A. Green, M. Mobius, J. J. Schmitt, and G. Boehm. 2007. Comparison of the structures of triacylglycerols from native and transgenic medium-chain fatty acid-enriched rape seed oil by liquid chromatography-atmospheric pressure chemical ionization ion-trap mass spectrometry (LC-APCI-ITMS). Lipids. 42: 383-394. (Pubitemid 46668933)
14. Rhee, E. P., S. Cheng, M. G. Larson, G. A. Walford, G. D. Lewis, E. McCabe, E. Yang, L. Farrell, C. S. Fox, C. J. O'Donnell, et al. 2011. Lipid profiling identifies a triacylglycerol signature of insulin resistance and improves diabetes prediction in humans. J. Clin. Invest. 121: 1402-1411.
15. Williams, J. P., M. U. Khan, and D. Wong. 1995. A simple technique for the analysis of positional distribution of fatty acids on di- and triacylglycerols using lipase and phospholipase A2. J. Lipid Res. 36: 1407-1412.
16. Angers, P., and J. Arul. 1999. A simple method for regiospecific analysis of triacylglycerols by gas chromatography. J. Am. Oil Chem. Soc. 76: 481-484.
17. Agren, J. J., and A. Kuksis. 2002. Analysis of diastereomeric DAG naphthylethylurethanes by normal-phase HPLC with on-line electrospray MS. Lipids. 37: 613-619. (Pubitemid 34734097)
18. van der Klift, E. J., G. Vivo-Truyols, F. W. Claassen, F. L. van Holthoon, and T. A. van Beek. 2008. Comprehensive two-dimensional liquid chromatography with ultraviolet, evaporative light scattering and mass spectrometric detection of triacylglycerols in corn oil. J. Chromatogr. A. 1178: 43-55. (Pubitemid 50007819)
19. Byrdwell, W. C., and W. E. Neff. 2002. Dual parallel electrospray ionization and atmospheric pressure chemical ionization mass spectrometry (MS), MS/MS and MS/MS/MS for the analysis of triacylglycerols and triacylglycerol oxidation products. Rapid Commun. Mass Spectrom. 16: 300-319.
20. Héron, S., M. Dreux, and A. Tchapla. 2004. Post-column addition as a method of controlling triacylglycerol response coefficient of an evaporative light scattering detector in liquid chromatography-evaporative light-scattering detection. J. Chromatogr. A. 1035: 221-225. (Pubitemid 38452301)
21. Cai, S. S., and J. A. Syage. 2006. Comparison of atmospheric pressure photoionization, atmospheric pressure chemical ionization, and electrospray ionization mass spectrometry for analysis of lipids. Anal. Chem. 78: 1191-1199.
22. Destaillats, F., M. de Wispelaere, F. Joffre, P. A. Golay, B. Hug, F. Giuffrida, L. Fauconnot, and F. Dionisi. 2006. Authenticity of milk fat by fast analysis of triacylglycerols. Application to the detection of partially hydrogenated vegetable oils. J. Chromatogr. A. 1131: 227-234. (Pubitemid 44508686)
23. Guyon, F., C. Absalon, A. Eloy, M. H. Salagoity, M. Esclapez, and B. Medina. 2003. Comparative study of matrix-assisted laser desorption/ionization and gas chromatography for quantitative determination of cocoa butter and cocoa butter equivalent triacylglycerol composition. Rapid Commun. Mass Spectrom. 17: 2317-2322. (Pubitemid 37243316)
24. Standal, I. B., D. E. Axelson, and M. Aursand. 2011. Authentication of marine oils using 13C NMR spectroscopy. Lipid Technology. 23: 152-154.
25. Danielewicz, M. A., L. A. Anderson, and A. K. Franz. 2011. Triacylglycerol profiling of marine microalgae by mass spectrometry. J. Lipid Res. 52: 2101-2108.
26. Standal, I. B., A. Prael, L. McEvoy, D. E. Axelson, and M. Aursand. 2007. Discrimination of cod liver oil according to wild/farmed and geographical origins by GC and 13 C NMR. J. Am. Oil Chem. Soc. 85: 105-112.
27. Andrikopoulos, N. K. 2002. Chromatographic and spectroscopic methods in the analysis of triacylglycerol species and regiospecific isomers of oils and fats. Crit. Rev. Food Sci. Nutr. 42: 473-505. (Pubitemid 39649738)
28. Kalo, P., A. Kemppinen, and V. Ollilainen. 2009. Determination of triacylglycerols in butterfat by normal-phase HPLC and electrospray-tandem mass spectrometry. Lipids. 44: 169-195.
29. Mangos, T. J., K. C. Jones, and T. A. Foglia. 1999. Normal-phase high performance liquid chromatographic separation and characterization of short- and long-chain triacylglycerols. Chromatographia. 49: 363-368. (Pubitemid 29205100)
30. Rocha, J. M., P. J. Kalo, V. Ollilainen, and F. X. Malcata. 2010. Separation and identification of neutral cereal lipids by normal phase high-performance liquid chromatography, using evaporative light-scattering and electrospray mass spectrometry for detection. J. Chromatogr. A. 1217: 3013-3025.
31. Adlof, R. O. 1995. Analysis of triacylglycerol positional isomers by solver ion high performance liquid chromatography. J. High Resol. Chromatogr. 18: 105-107.
32. Christie, W. W. 1994. Silver ion and chiral chromatography in the analysis of triacylglycerols. Prog. Lipid Res. 33: 9-18. (Pubitemid 24106634)
33. Holcapek, M., H. Velinska, M. Lisa, and P. Cesla. 2009. Orthogonality of silver-ion and non-aqueous reversed-phase HPLC/MS in the analysis of complex natural mixtures of triacylglycerols. J. Sep. Sci. 32: 3672-3680.
34. Holčapek, M., H. Dvorakova, M. Lisa, A. J. Giron, P. Sandra, and J. Cvacka. 2010. Regioisomeric analysis of triacylglycerols using silver-ion liquid chromatography-atmospheric pressure chemical ionization mass spectrometry: comparison of five different mass analyzers. J. Chromatogr. A. 1217: 8186-8194.
35. Cvacka, J., E. Krafkova, P. Jiros, and I. Valterova. 2006. Computer-assisted interpretation of atmospheric pressure chemical ionization mass spectra of triacylglycerols. Rapid Commun. Mass Spectrom. 20: 3586-3594. (Pubitemid 44871316)
36. Fauconnot, L., J. Hau, J. M. Aeschlimann, L. B. Fay, and F. Dionisi. 2004. Quantitative analysis of triacylglycerol regioisomers in fats and oils using reversed-phase high-performance liquid chromatography and atmospheric pressure chemical ionization mass spectrometry. Rapid Commun. Mass Spectrom. 18: 218-224. (Pubitemid 38160359)
37. Acheampong, A., N. Leveque, A. Tchapla, and S. Heron. 2011. Simple complementary liquid chromatography and mass spectrometry approaches for the characterization of triacylglycerols in Pinus koraiensis seed oil. J. Chromatogr. A. 1218: 5087-5100.
38. Fasciotti, M., and A. D. Pereira Netto. 2010. Optimization and application of methods of triacylglycerol evaluation for characterization of olive oil adulteration by soybean oil with HPLC-APCI-MS-MS. Talanta. 81: 1116-1125.
39. Malone, M., and J. J. Evans. 2004. Determining the relative amounts of positional isomers in complex mixtures of triglycerides using reversed-phase high-performance liquid chromatography-tandem mass spectrometry. Lipids. 39: 273-284. (Pubitemid 38738139)
40. Leskinen, H., J. P. Suomela, J. Pinta, and H. Kallio. 2008. Regioisomeric structure determination of alpha- and gamma-linolenoyldilinoleoylglycerol in blackcurrant seed oil by silver ion high-performance liquid chromatography and mass spectrometry. Anal. Chem. 80: 5788-5793.
41. Takáts, Z., J. M. Wiseman, B. Gologan, and R. G. Cooks. 2004. Mass spectrometry sampling under ambient conditions with desorption electrospray ionization. Science. 306: 471-473. (Pubitemid 39372443)
42. Gerbig, S., and Z. Takats. 2010. Analysis of triglycerides in food items by desorption electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 24: 2186-2192.
43. Cody, R. B., J. A. Laramee, and H. D. Durst. 2005. Versatile new ion source for the analysis of materials in open air under ambient conditions. Anal. Chem. 77: 2297-2302. (Pubitemid 40562727)
44. Vaclavik, L., V. Hrbek, T. Cajka, B. A. Rohlik, P. Pipek, and J. Hajslova. 2011. Authentication of animal fats using direct analysis in real time (DART) ionization-mass spectrometry and chemometric tools. J. Agric. Food Chem. 59: 5919-5926.
45. Sampson, J. S., A. M. Hawkridge, and D. C. Muddiman. 2006. Generation and detection of multiply-charged peptides and proteins by matrix-assisted laser desorption electrospray ionization (MALDESI) Fourier transform ion cyclotron resonance mass spectrometry. J. Am. Soc. Mass Spectrom. 17: 1712-1716. (Pubitemid 44809956)
46. McEwen, C. N., R. G. McKay, and B. S. Larsen. 2005. Analysis of solids, liquids, and biological tissues using solids probe introduction at atmospheric pressure on commercial LC/MS instruments. Anal. Chem. 77: 7826-7831. (Pubitemid 41746252)
47. Chen, H., A. Wortmann, W. Zhang, and R. Zenobi. 2007. Rapid in vivo fingerprinting of nonvolatile compounds in breath by extractive electrospray ionization quadrupole time-of-flight mass spectrometry. Angew. Chem. Int. Ed. Engl. 46: 580-583. (Pubitemid 46159202)
48. Haapala, M., J. Pol, V. Saarela, V. Arvola, T. Kotiaho, R. A. Ketola, S. Franssila, T. J. Kauppila, and R. Kostiainen. 2007. Desorption atmospheric pressure photoionization. Anal. Chem. 79: 7867-7872. (Pubitemid 47622418)
49. Alberici, L. C., H. C. Oliveira, R. R. Catharino, A. E. Vercesi, M. N. Eberlin, and R. M. Alberici. 2011. Distinct hepatic lipid profile of hypertriglyceridemic mice determined by easy ambient sonicspray ionization mass spectrometry. Anal. Bioanal. Chem. 401: 1651-1659.
50. Simas, R. C., R. R. Catharino, I. B. Cunha, E. C. Cabral, D. Barrera-Arellano, M. N. Eberlin, and R. M. Alberici. 2010. Instantaneous characterization of vegetable oils via TAG and FFA profiles by easy ambient sonic-spray ionization mass spectrometry. Analyst. 135: 738-744.
51. Haddad, R., R. Sparrapan, T. Kotiaho, and M. N. Eberlin. 2008. Easy ambient sonic-spray ionization-membrane interface mass spectrometry for direct analysis of solution constituents. Anal. Chem. 80: 898-903. (Pubitemid 351206883)
52. Chapagain, B. P., and Z. Wiesman. 2009. MALDI-TOF/MS fingerprinting of triacylglycerols (TAGs) in olive oils produced in the Israeli Negev desert. J. Agric. Food Chem. 57: 1135-1142.
53. Mottram, H. R., and R. P. Evershed. 2001. Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J. Chromatogr. A. 926: 239-253. (Pubitemid 32744729)
54. Mottram, H. R., Z. M. Crossman, and R. P. Evershed. 2001. Regiospecific characterisation of the triacylglycerols in animal fats using high performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. Analyst. 126: 1018-1024. (Pubitemid 32673281)
55. Hsu, F. F., and J. Turk. 2010. Electrospray ionization multiple-stage linear ion-trap mass spectrometry for structural elucidation of triacylglycerols: assignment of fatty acyl groups on the glycerol backbone and location of double bonds. J. Am. Soc. Mass Spectrom. 21: 657-669.
56. Herrera, L. C., M. A. Potvin, and J. E. Melanson. 2010. Quantitative analysis of positional isomers of triacylglycerols via electrospray ionization tandem mass spectrometry of sodiated adducts. Rapid Commun. Mass Spectrom. 24: 2745-2752.
57. Kemppinen, A., and P. Kalo. 2006. Quantification of triacylglycerols in butterfat by gas chromatography-electron impact mass spectrometry using molar correction factors for [M-RCOO]+ ions. J. Chromatogr. A. 1134: 260-283. (Pubitemid 44633937)
58. Hvattum, E. 2001. Analysis of triacylglycerols with non-aqueous re-versed- phase liquid chromatography and positive ion electrospray tandem mass spectrometry. Rapid Commun. Mass Spectrom. 15: 187-190. (Pubitemid 32148400)
59. Marzilli, L. A., L. B. Fay, F. Dionisi, and P. Vouros. 2003. Structural characterization of triacylglycerols using electrospray ionization- MSn ion-trap MS. J. Am. Oil Chem. Soc. 80: 195-202.
60. Zeng, Y. X., P. Araujo, Z. Y. Du, T. T. Nguyen, L. Froyland, and B. Grung. 2010. Elucidation of triacylglycerols in cod liver oil by liquid chromatography electrospray tandem ion-trap mass spectrometry. Talanta. 82: 1261-1270.
61. Fauconnot, L., J. M. Aeschlimann, and F. Dionisi. 2004. Triacylglycerol structure and composition of oils containing LC-PUFA using RP-HPLC and APCI-MS. Lipid Technology. 16: 134-137.
62. Byrdwell, W. C., E. A. Emken, W. E. Neff, and R. O. Adlof. 1996. Quantitative analysis of triglycerides using atmospheric pressure chemical ionization-mass spectrometry. Lipids. 31: 919-935.
63. Leskinen, H. M., J. P. Suomela, and H. P. Kallio. 2010. Quantification of triacylglycerol regioisomers by ultra-high-performance liquid chromatography and ammonia negative ion atmospheric pressure chemical ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 24: 1-5.
64. Leskinen, H., J. P. Suomela, and H. Kallio. 2007. Quantification of triacylglycerol regioisomers in oils and fat using different mass spectrometric and liquid chromatographic methods. Rapid Commun. Mass Spectrom. 21: 2361-2373. (Pubitemid 47121168)
65. McClellan, J. E., J. P. Murphy III, J. J. Mulholland, and R. A. Yost. 2002. Effects of fragile ions on mass resolution and on isolation for tandem mass spectrometry in the quadrupole ion trap mass spectrometer. Anal. Chem. 74: 402-412. (Pubitemid 34072707)
66. Breckenridge, W. C., and A. Kuksis. 1968. Specific distribution of short-chain fatty acids in molecular distillates of bovine milk fat. J. Lipid Res. 9: 388-393.
67. Breckenridge, W. C., and A. Kuksis. 1968. Structure of bovine milk fat triglycerides: I. Short and medium chain lengths. Lipids. 3: 291-300.
68. Thomas, M. C., T. W. Mitchell, D. G. Harman, J. M. Deeley, J. R. Nealon, and S. J. Blanksby. 2008. Ozone-induced dissociation: elucidation of double bond position within mass-selected lipid ions. Anal. Chem. 80: 303-311. (Pubitemid 351448435)